Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The Whiskey lactones

You must have Java installed to view the molecular visualization on this page
Photo by permission of M. Roudintska - Art & Parfum

(3S,4S)-(-)-4-butyl-3-methylbutan-4-olide - faint coconut note, faint musty, earthy, remeniscant of hay

Odor Threshold = 20-24 ppb in white wine (R.C. Brown)

Odor Threshold = 54-57 ppb in red wine (R.C. Brown)

= (4S,5S)-5-butyl-4-methyldihydrofuran-2(3H)-one

Also known as (4S,5S)-(-)-whiskey lactone

Also known as (4S,5S)-(-)-oak lactone

Ref: A. Mosandl, W. Deger, M. Gessner, C. Gunther, G. Heusinger and G. Singer, Lebensmittelchem Gerichte Chem. 41, 35 (1987); B. Koppenhoefer, et. al., Perfumer & Flavorist, Vol. 19, No. 5, 1-14, 1994; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007

(3R,4R)-(+)-4-butyl-3-methylbutan-4-olide - sweet woody, bright fresh coconut note

Odor Threshold = 132 ppb in white wine (R.C. Brown)

Odor Threshold = 170-175 ppb in red wine (R.C. Brown)

= (4R,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one

Also known as (4R,5R)- -(+)-whiskey lactone

Also known as (4R,5R)- -(+)-oak lactone

Ref: A. Mosandl, W. Deger, M. Gessner, C. Gunther, G. Heusinger and G. Singer, Lebensmittelchem Gerichte Chem. 41, 35 (1987); B. Koppenhoefer, et. al., Perfumer & Flavorist, Vol. 19, No. 5, 1-14, 1994; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007

(3R,4S)-(-)-4-butyl-3-methylbutan-4-olide -strong coconut note, reminiscent of celery

Odor Threshold = 305-330 ppb in white wine (R.C. Brown)

Odor Threshold = 285-305 ppb in red wine (R.C. Brown)

= (4R,5S)-5-butyl-4-methyldihydrofuran-2(3H)-one

Also known as (4R,5S)-(-)-whiskey lactone

Also known as (4R,5S)-(-)-oak lactone

Ref: A. Mosandl, W. Deger, M. Gessner, C. Gunther, G. Heusinger and G. Singer, Lebensmittelchem Gerichte Chem. 41, 35 (1987); B. Koppenhoefer, et. al., Perfumer & Flavorist, Vol. 19, No. 5, 1-14, 1994; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007

(3S,4R)-(+)-4-butyl-3-methylbutan-4-olide - piquant celery note, faint coconut note, green walnut note

Odor Threshold = 140-172 ppb in white wine (R.C. Brown)

Odor Threshold = 370-380 ppb in red wine (R.C. Brown)

= (4S,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one

Also known as (4S,5R)-(+)-whiskey lactone

Also known as (4S,5R)-(+)-whiskey lactone

Ref: A. Mosandl, W. Deger, M. Gessner, C. Gunther, G. Heusinger and G. Singer, Lebensmittelchem Gerichte Chem. 41, 35 (1987); B. Koppenhoefer, et. al., Perfumer & Flavorist, Vol. 19, No. 5, 1-14, 1994; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

HOME

Copyright 2001-2002 - Leffingwell & Associates